How to specify the structure of substituted blade-like zigzag diamondoids

Research output: Journal contributionsJournal articlesResearchpeer-review

Authors

The dualist of an [n]diamondoid consists of vertices situated in the centers of each of the n adamantane units, and of edges connecting vertices corresponding to units sharing a chair-shaped hexagon of carbon atoms. Since the polycyclic structure of diamondoids is rather complex, so is their nomenclature. For specifying chemical constitution or isomerism of all diamondoids the Balaban-Schleyer graph-theoretical approach based on dualists has been generally adopted. However, when one needs to indicate the location of C and H atoms or of a substituent in a diamondoid or the stereochemical relationships between substituents, only the IUPAC polycycle nomenclature (von Baeyer nomenclature) provides the unique solution. This is so since each IUPAC name is associated with a unique atom numbering scheme. Diamondoids are classified into catamantanes (which can be regular or irregular), perimantanes, and coronamantanes. Regular catamantanes have molecular formulas C 4n+6H4n+12. Among regular catamantanes, the rigid blade-shaped zigzag catamantanes (so called because their dualists consist of a zigzag line with a code of alternating digits 1 and 2) exhibit a simple pattern in their von Baeyer nomenclature. Their carbon atoms form a main ring with 4n + 4 atoms, and the remaining atoms form two 1-carbon bridges. All zigzag [n]catamantanes with n > 2 have quaternary carbon atoms, and the first bridgehead in the main ring is such an atom. Their partitioned formula is C n-2(CH)2n+4(CH2) n+4. As a function of their parity, IUPAC names based on the von Baeyer approach have been devised for all zigzag catamantanes, allowing the unique location for every C and H atom. The dualist of such a zigzag catamantane defines a plane bisecting the molecule, and the stereochemical features of hydrogens attached to secondary carbon atoms can be specified relatively to that plane. © 2013 Versita Warsaw and Springer-Verlag Wien.
Original languageEnglish
JournalCentral European Journal of Chemistry
Volume11
Issue number9
Pages (from-to)1423-1430
Number of pages8
ISSN1895-1066
DOIs
Publication statusPublished - 09.2013

    Research areas

  • Chemistry - Catamantanes, Diamondoids, Dualists, IUPAC nomenclature

Documents

DOI

Recently viewed

Publications

  1. Embedded, not plugged-in
  2. Aligning the design of intermediary organisations with the ecosystem
  3. Lab-scale experiment of a closed thermochemical heat storage system including honeycomb heat exchanger
  4. Children's interpretation of ambiguous pronouns based on prior discourse
  5. Søren Kierkegaard in deutscher Sprache
  6. Managing Green Business Model Transformations
  7. Comparative observations, empirical findings and research perspectives
  8. A Model Based Feedforward Regulator Improving PI Control of an Ice-Clamping Device Activated by Thermoelectric Cooler
  9. An Indirectly Controlled Full Variable Valve Train System to Improve the Internal Combustion Phase Engines
  10. John Howard Yoder
  11. Nanoindentation of Poly(Ethylene Oxide) Nanofibers by Atomic Force Microscope (AFM)
  12. A Theory-Based Teaching Concept To Embed Sustainability In The Engineering Curriculum
  13. Life satisfaction in Germany after reunification: Additional insights on the pattern of convergence
  14. Inquiry-based Learning Environments to Welcome the Diversity of a Chemistry Class
  15. It Matters to Whom You Compare Yourself
  16. Learning Strategies of First Year University Students
  17. Uncertainty, Pluralism, and the Knowledge-based Theory of the Firm
  18. Exploring complex phenomena with qualitative research methods
  19. Encoding the law of State responsibility with courage and resolve
  20. The Measurement of Grip-Strength in Automobiles
  21. Non-native populations of an invasive tree outperform their native conspecifics
  22. ... address unknown?
  23. Ownership Patterns and Enterprise Groups in German Structural Business Statistics
  24. The Transition to Renewable Energy Systems - On the Way to a Comprehensive Transition Concept
  25. Exploring the Capacity of Water Framework Directive Indices to Assess Ecosystem Services in Fluvial and Riparian Systems
  26. Political discourse as mediated and public discourse